The scope of sustained military operations in Iraq and Afghanistan has placed great demands on the Armed Forces of the United States, and accordingly, military families have been faced with deployments in more rapid succession than ever before. When military parents fulfill occupational duties during wartime, military children and families face multiple challenges, including extended separations, disruptions in family routines, and potentially compromised parenting related to traumatic exposure and subsequent mental health problems. Such challenges can begin to exert a significant toll on the well-being of both individuals and relationships (e.g., marital, parent–child) within military families. In order to respond more effectively to the needs of military families, it is essential that mental health clinicians and researchers have a better understanding of the challenges faced by military families throughout the entire deployment experience and the ways in which these challenges may have a cumulative impact over multiple deployments. Moreover, the mental health field must become better prepared to support service members and families across a rapidly evolving landscape of military operations around the world, including those who are making the transition from active duty to Veteran status and navigating a return to civilian life and those families in which parents will continue to actively serve and deploy in combat zones. In this article, we utilize family systems and ecological perspectives to advance our understanding of how military families negotiate repeated deployment experiences and how such experiences impact the well-being and adjustment of families at the individual, dyadic, and whole family level.